AU2004299316B2 - Prostaglandin synthesis - Google Patents
Prostaglandin synthesis Download PDFInfo
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- AU2004299316B2 AU2004299316B2 AU2004299316A AU2004299316A AU2004299316B2 AU 2004299316 B2 AU2004299316 B2 AU 2004299316B2 AU 2004299316 A AU2004299316 A AU 2004299316A AU 2004299316 A AU2004299316 A AU 2004299316A AU 2004299316 B2 AU2004299316 B2 AU 2004299316B2
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- 150000003180 prostaglandins Chemical class 0.000 title description 11
- 230000015572 biosynthetic process Effects 0.000 title description 7
- 238000003786 synthesis reaction Methods 0.000 title description 7
- 238000000034 method Methods 0.000 claims abstract description 67
- 125000001424 substituent group Chemical group 0.000 claims abstract description 25
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 12
- -1 prostaglandin compounds Chemical class 0.000 claims abstract description 10
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 10
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 149
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 108
- 102100034195 Thrombopoietin Human genes 0.000 claims description 76
- 101000799461 Homo sapiens Thrombopoietin Proteins 0.000 claims description 72
- SXXLKZCNJHJYFL-UHFFFAOYSA-N 4,5,6,7-tetrahydro-[1,2]oxazolo[4,5-c]pyridin-5-ium-3-olate Chemical compound C1CNCC2=C1ONC2=O SXXLKZCNJHJYFL-UHFFFAOYSA-N 0.000 claims description 64
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 239000003153 chemical reaction reagent Substances 0.000 claims description 21
- 150000002009 diols Chemical class 0.000 claims description 19
- 125000006239 protecting group Chemical group 0.000 claims description 17
- 238000003776 cleavage reaction Methods 0.000 claims description 16
- 230000007017 scission Effects 0.000 claims description 16
- 238000005906 dihydroxylation reaction Methods 0.000 claims description 15
- 238000010511 deprotection reaction Methods 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- GGXICVAJURFBLW-CEYXHVGTSA-N latanoprost Chemical compound CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1 GGXICVAJURFBLW-CEYXHVGTSA-N 0.000 claims description 13
- 230000032050 esterification Effects 0.000 claims description 11
- 238000005886 esterification reaction Methods 0.000 claims description 11
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- 238000007239 Wittig reaction Methods 0.000 claims description 10
- 230000009435 amidation Effects 0.000 claims description 10
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- AQOKCDNYWBIDND-FTOWTWDKSA-N bimatoprost Chemical compound CCNC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=CC=C1 AQOKCDNYWBIDND-FTOWTWDKSA-N 0.000 claims description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- 238000007259 addition reaction Methods 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- MNZAKDODWSQONA-UHFFFAOYSA-N 1-dibutylphosphorylbutane Chemical compound CCCCP(=O)(CCCC)CCCC MNZAKDODWSQONA-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000012044 organic layer Substances 0.000 description 21
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
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- 150000002148 esters Chemical class 0.000 description 15
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical group CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 14
- 125000005843 halogen group Chemical group 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 239000000523 sample Substances 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
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- 238000005481 NMR spectroscopy Methods 0.000 description 9
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 8
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical group CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
- 241000872931 Myoporum sandwicense Species 0.000 description 6
- 238000013019 agitation Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 5
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
- 238000011916 stereoselective reduction Methods 0.000 description 5
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- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 4
- 229940006138 antiglaucoma drug and miotics prostaglandin analogues Drugs 0.000 description 4
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- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 4
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- HJRHGQQOWINKNO-UHFFFAOYSA-N 4-carboxybutylphosphanium;bromide Chemical compound [Br-].OC(=O)CCCC[PH3+] HJRHGQQOWINKNO-UHFFFAOYSA-N 0.000 description 3
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- IOIHFHNPXJFODN-UHFFFAOYSA-M tetrakis(hydroxymethyl)phosphanium;hydroxide Chemical compound [OH-].OC[P+](CO)(CO)CO IOIHFHNPXJFODN-UHFFFAOYSA-M 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- PGOLTJPQCISRTO-UHFFFAOYSA-N vinyllithium Chemical compound [Li]C=C PGOLTJPQCISRTO-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0016—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing only hydroxy, etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2011200763A AU2011200763B2 (en) | 2003-12-19 | 2011-02-23 | Prostaglandin synthesis |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0329379.2 | 2003-12-19 | ||
GBGB0329379.2A GB0329379D0 (en) | 2003-12-19 | 2003-12-19 | Prostaglandin synthesis |
PCT/GB2004/005028 WO2005058812A2 (fr) | 2003-12-19 | 2004-12-01 | Synthese de la prostaglandine |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2011200763A Division AU2011200763B2 (en) | 2003-12-19 | 2011-02-23 | Prostaglandin synthesis |
Publications (2)
Publication Number | Publication Date |
---|---|
AU2004299316A1 AU2004299316A1 (en) | 2005-06-30 |
AU2004299316B2 true AU2004299316B2 (en) | 2011-01-06 |
Family
ID=30471335
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2004299316A Active AU2004299316B2 (en) | 2003-12-19 | 2004-12-01 | Prostaglandin synthesis |
AU2011200763A Active AU2011200763B2 (en) | 2003-12-19 | 2011-02-23 | Prostaglandin synthesis |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2011200763A Active AU2011200763B2 (en) | 2003-12-19 | 2011-02-23 | Prostaglandin synthesis |
Country Status (14)
Country | Link |
---|---|
EP (1) | EP1694641B1 (fr) |
JP (3) | JP4764828B2 (fr) |
KR (1) | KR20060118555A (fr) |
CN (2) | CN1894209B (fr) |
AT (1) | ATE428693T1 (fr) |
AU (2) | AU2004299316B2 (fr) |
CA (2) | CA2549056C (fr) |
CZ (1) | CZ305964B6 (fr) |
DE (1) | DE602004020667D1 (fr) |
DK (1) | DK1694641T3 (fr) |
ES (1) | ES2325266T3 (fr) |
GB (1) | GB0329379D0 (fr) |
IL (2) | IL175940A (fr) |
WO (1) | WO2005058812A2 (fr) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008037782A (ja) * | 2006-08-04 | 2008-02-21 | Daiichi Fine Chemical Co Ltd | プロスタグランジン誘導体の製造方法 |
US7642370B2 (en) | 2006-08-07 | 2010-01-05 | Daiichi Fine Chemical Co., Ltd. | Method for preparing prostaglandin derivative |
AR071312A1 (es) * | 2008-04-09 | 2010-06-09 | Scinopharm Taiwan Ltd | Proceso para la preparacion de analogos de prostaglandina y sus intermediarios |
EP2135860A1 (fr) * | 2008-06-20 | 2009-12-23 | Sandoz AG | Procédé amélioré pour la production de Bimatoprost |
WO2011008756A1 (fr) | 2009-07-13 | 2011-01-20 | Irix Pharmaceuticals | Synthèse de prostanoïdes |
CN102050772B (zh) * | 2009-11-02 | 2013-08-21 | 上海天伟生物制药有限公司 | 一种比马前列素晶体及其制备方法和用途 |
US9238621B2 (en) * | 2011-06-02 | 2016-01-19 | Chinoin Zrt | Processes for the preparation of prostaglandin amides |
HU231203B1 (hu) * | 2011-12-21 | 2021-10-28 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Új eljárás travoprost előállítására |
WO2013133730A1 (fr) * | 2012-03-09 | 2013-09-12 | Instytut Farmaceutyczny | Procédé de préparation d'analogues de prostaglandine f2α |
EP2911623B1 (fr) | 2012-10-26 | 2019-08-14 | Forsight Vision5, Inc. | Système ophtalmique pour la libération prolongée de médicament dans l' oeil |
US10100028B2 (en) | 2013-09-30 | 2018-10-16 | Patheon Api Services Inc. | Synthesis routes for prostaglandins and prostaglandin intermediates using metathesis |
US20160296532A1 (en) | 2015-04-13 | 2016-10-13 | Forsight Vision5, Inc. | Ocular Insert Composition of a Semi-Crystalline or Crystalline Pharmaceutically Active Agent |
EP3235810A1 (fr) | 2016-04-19 | 2017-10-25 | Gentec, S.A. | Procédé pour la préparation de bimatoprost |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030187071A1 (en) * | 2001-07-17 | 2003-10-02 | Henegar Kevin E. | Process and intermediates to prepare latanoprost |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1582853A (en) * | 1977-06-16 | 1981-01-14 | Ici Ltd | Prostane derivatives |
JPS562979A (en) * | 1979-06-19 | 1981-01-13 | Ono Pharmaceut Co Ltd | Prostaglandin i2 analog compound, its preparation, and pharmaceutical composition containing the same |
JPS57171965A (en) * | 1981-04-15 | 1982-10-22 | Teijin Ltd | Novel prostaglandin intermediate and its preparation |
US4708966A (en) * | 1986-06-27 | 1987-11-24 | The Procter & Gamble Company | Novel anti-inflammatory agents, pharmaceutical compositions and methods for reducing inflammation |
JPS63188687A (ja) * | 1987-01-30 | 1988-08-04 | Sagami Chem Res Center | 有機ケイ素化合物の製造方法 |
JP2536026B2 (ja) * | 1988-03-10 | 1996-09-18 | 史衛 佐藤 | α,β―置換シクロペンタノン誘導体の製造法 |
US5698733A (en) * | 1994-09-30 | 1997-12-16 | Alcon Laboratories, Inc. | Use of 9-deoxy prostaglandin derivatives to treat glaucoma |
US6015922A (en) * | 1997-12-19 | 2000-01-18 | Alcon Laboratories, Inc. | N-alkyl-N-alkoxycarboxamides and methods of use in prostaglandin synthesis |
GB9908327D0 (en) * | 1999-04-12 | 1999-06-09 | Chirotech Technology Ltd | Process for the preparation of prostaglandin precursors |
AU770343B2 (en) * | 1999-09-06 | 2004-02-19 | Fumie Sato | Prostaglandin E analogues |
WO2003008368A1 (fr) * | 2001-07-17 | 2003-01-30 | Pharmacia & Upjohn Company | Procede et produits intermediaires utilises pour produire du latanoprost |
-
2003
- 2003-12-19 GB GBGB0329379.2A patent/GB0329379D0/en not_active Ceased
-
2004
- 2004-12-01 AT AT04801246T patent/ATE428693T1/de active
- 2004-12-01 AU AU2004299316A patent/AU2004299316B2/en active Active
- 2004-12-01 CA CA2549056A patent/CA2549056C/fr active Active
- 2004-12-01 CN CN2004800379243A patent/CN1894209B/zh active Active
- 2004-12-01 DE DE602004020667T patent/DE602004020667D1/de active Active
- 2004-12-01 WO PCT/GB2004/005028 patent/WO2005058812A2/fr active Application Filing
- 2004-12-01 DK DK04801246T patent/DK1694641T3/da active
- 2004-12-01 EP EP04801246A patent/EP1694641B1/fr active Active
- 2004-12-01 CN CN2009100028542A patent/CN101486699B/zh active Active
- 2004-12-01 CZ CZ2006-386A patent/CZ305964B6/cs unknown
- 2004-12-01 JP JP2006544532A patent/JP4764828B2/ja active Active
- 2004-12-01 CA CA2854783A patent/CA2854783C/fr active Active
- 2004-12-01 ES ES04801246T patent/ES2325266T3/es active Active
- 2004-12-01 KR KR1020067012014A patent/KR20060118555A/ko not_active Application Discontinuation
-
2006
- 2006-05-25 IL IL175940A patent/IL175940A/en active IP Right Grant
-
2011
- 2011-02-23 AU AU2011200763A patent/AU2011200763B2/en active Active
- 2011-04-15 JP JP2011091348A patent/JP5653827B2/ja active Active
-
2012
- 2012-01-22 IL IL217670A patent/IL217670A/en active IP Right Grant
-
2013
- 2013-07-03 JP JP2013140108A patent/JP5795354B2/ja active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030187071A1 (en) * | 2001-07-17 | 2003-10-02 | Henegar Kevin E. | Process and intermediates to prepare latanoprost |
Non-Patent Citations (2)
Title |
---|
Fox M.E. et al, Advanced Synthesis and Catalysis, 2002, vol 344, pp. 50-56 * |
Maruyama T. et al, Bioorganic and Medicinal Chemistry, 2002, vol. 10, pp. 975-988 * |
Also Published As
Publication number | Publication date |
---|---|
JP2011201883A (ja) | 2011-10-13 |
JP2007517780A (ja) | 2007-07-05 |
KR20060118555A (ko) | 2006-11-23 |
WO2005058812A2 (fr) | 2005-06-30 |
JP5795354B2 (ja) | 2015-10-14 |
CA2549056A1 (fr) | 2005-06-30 |
ATE428693T1 (de) | 2009-05-15 |
ES2325266T3 (es) | 2009-08-31 |
CN1894209A (zh) | 2007-01-10 |
CA2854783C (fr) | 2017-01-10 |
IL217670A (en) | 2013-02-28 |
CA2854783A1 (fr) | 2005-06-30 |
CN101486699B (zh) | 2012-06-27 |
JP5653827B2 (ja) | 2015-01-14 |
IL175940A0 (en) | 2006-10-05 |
CA2549056C (fr) | 2014-09-02 |
AU2011200763B2 (en) | 2013-05-30 |
CZ305964B6 (cs) | 2016-05-25 |
JP4764828B2 (ja) | 2011-09-07 |
CZ2006386A3 (cs) | 2006-11-15 |
DE602004020667D1 (en) | 2009-05-28 |
AU2011200763A1 (en) | 2011-03-17 |
EP1694641A2 (fr) | 2006-08-30 |
WO2005058812A3 (fr) | 2005-10-13 |
IL175940A (en) | 2012-05-31 |
EP1694641B1 (fr) | 2009-04-15 |
DK1694641T3 (da) | 2009-07-20 |
GB0329379D0 (en) | 2004-01-21 |
JP2013231053A (ja) | 2013-11-14 |
AU2004299316A1 (en) | 2005-06-30 |
CN1894209B (zh) | 2010-12-22 |
CN101486699A (zh) | 2009-07-22 |
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Legal Events
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FGA | Letters patent sealed or granted (standard patent) | ||
PC | Assignment registered |
Owner name: MACFARLAN SMITH LIMITED Free format text: FORMER OWNER(S): JOHNSON MATTHEY PUBLIC LIMITED COMPANY |